Holiday Special: 2025 Lessons, Risky Bets, and an Alaska Surprise (BONUS EP)

About this episode

A big thanks to our friend Joe Saul-Sehy for inviting us to join an episode of Stacking Benjamins – we had a blast, and we think you'll enjoy this convo as well!

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It's the most wonderful time of the year in the basement, and we're kicking off the holiday season with our biggest, most packed episode yet.

Joe Saul-Sehy, OG, and Neighbor Doug welcome Joel Larsgaard and Matt Altmix from the How to Money podcast for a year-end celebration of everything that mattered in money during 2025. Think of this as the holiday parade of personal finance episodes. There's a lot happening, it's all connected, and you'll want to stick around for the whole thing.

First up, Joel and Matt join the crew for their Top 5 Lessons from the Events of 2025. From AI's real impact on everyday work to market surprises nobody saw coming, this segment unpacks the money moments that actually changed how we think about our finances. These aren't just headlines rehashed. They're the insights that'll help you make smarter moves in 2026.

Then the show shifts to a fascinating trend everyone's noticing but nobody's quite figured out yet. Why is everyone suddenly betting on everything? Prediction markets are exploding, retail investors are taking bigger risks, and the line between investing and gambling feels blurrier than ever. Joe, OG, Joel, and Matt dig into what's driving this shift, whether it's brilliant or reckless, and how to think about risk when it seems like the whole world just discovered the casino.

But wait, there's more. Nick from Alaska calls in with a real-world budgeting challenge that proves even the most prepared Stackers face seasonal money surprises. His situation sparks the kind of practical, helpful conversation this show does best.

And because this is a holiday kickoff episode, we're wrapping with big news about the Stacking Benjamins Vault, the new tool designed to help you organize and protect your most important financial documents without the headache.

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Best friends out!

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